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Formaldehyde → Dimethyl 4-(2,6-dichlorophenyl)-6-(2-phenylethyl)-2-(1-oxo-1-methoxy-2-propen-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 343311
ノート
印刷プレビュー

反応式

HRID 343311 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:12][C:11]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[C:10]1[C:32]([O:34][CH3:35])=[O:33].[CH3:36]N1CCNCC1.C=O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:12][C:11]([C:27](=[CH2:36])[C:28](=[O:29])[O:30][CH3:31])=[C:10]1[C:32]([O:34][CH3:35])=[O:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 70203360Dimethyl 4-(2,6-dichlorophenyl)-2-methoxycarbonylmethyl-6-(2-phenylethyl)-1,4-dihydropyridine-3,5-dicarboxylate

生成物 1

HCID 131721086Dimethyl 4-(2,6-dichlorophenyl)-6-(2-phenylethyl)-2-(1-oxo-1-methoxy-2-propen-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate収率 50.9%

試薬・触媒・溶媒 1

HCID 176
Acetic Acid
溶媒

実験手順

Dimethyl 4-(2,6-dichlorophenyl)-2-methoxycarbonylmethyl-6-[2-(phenyl)ethyl]-1,4-dihydropyridine-3,5-dicarboxylate (588 mg, 1.135 m mol) and N-methylpiperazine (0.132 ml, 1.19 m mol) were dissolved in acetic acid (3 ml) and to the solution was added paraformaldehyde. The mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo and partitioned between CH2Cl2 (50 ml) and aqueous NaHCO3 solution (20 ml). The aqueous layer was extracted with CH2Cl2 (30 ml). The combined organic layer and the extract were washed with brine (10 ml), dried (MgSO4), and concentrated in vacuo to give a yellow oil. This was crystallized from ethyl acetate and isopropyl ether gave a yellow solid (270 mg, 50.9%). Second crop was obtained from the mother liquid (78 mg, 14.7%). 1H NMR (D2O) δ7.35-7.16 (m, 7H), 7-05-6.97 (m, 1H), 6.21 (br.s, 1H), 6.06 (s, 1H), 5.52 (br.s, 1H), 5.43 (br.s, 1H), 3.73 (s, 3H), 3.57 (s, 3H), 3.46 (s, 3H), 3.10-2.80 (m, 4H).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between CH2Cl2 (50 ml) and aqueous NaHCO3 solution (20 ml)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (30 ml)
  4. washThe combined organic layer and the extract were washed with brine (10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThis was crystallized from ethyl acetate and isopropyl ether

出典と根拠

ORDレコード
ord-f6bb277c56ab4a1a90411bd579598096
出典データセット
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05861402

反応ノート

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